478: From Pro Snowboarder to Full-Time Flipper & Investor w/ Chris Naugle

The path of a wealthy real estate investor is never a straight line. Often we’ll set up goals we deem worth chasing, then somewhere along the way, we’ll pivot to a more refined goal. Without knowing where we want to go, we can’t get the proper footing to start the journey. This is exactly what snowboarder, skater, real estate investor, and lender, Chris Naugle, talks about with us today.

Chris grew up in chilly Buffalo, New York and knew he wasn’t the employment type of guy. So, after quitting his first job, he decided to start a clothing company in his basement. Then, with some of the profits from his clothing venture, paired with a loan from his mom’s equity line, he opened up a skateboard shop. Everything was going well, until the dot com crash, prompting him to become an advisor on Wall Street.

As an advisor, Chris found that more and more of his wealthy clients were investing in real estate. This prompted him to take the leap and start flipping, buying commercial real estate, and investing in rentals. But, Chris wasn’t borrowing the right way, leading him to have to get rid of his 37 unit portfolio or go bankrupt.

After losing years' worth of work and a massive amount of equity, Chris started to draw up systems and procedures that could work as a safety net for his investments. Now with a smaller portfolio of around 23 units, he works mostly as the bank that lends other investors their money. All of this was made possible when Chris stopped and thought about what his “perfect day” was and what he needed to do to make it a reality.

In This Episode We Cover:

Using flipping as an entry point to get into real estate investing

Buying commercial buildings like strip malls

Keeping your debt-to-income (DTI) low so you can keep borrowing

Conventional financing vs. commercial financing for real estate investing

The “rules of engagement” when it comes to investing

Trading money for money instead of time for money

Knowing what your “perfect day” is

And SO much more!

Links from the Show

BiggerPockets Forums

BiggerPockets Youtube Channel